May 25, 2018

A timeline enumerating my experiences in the world of technology.


My mother and I move from Louisiana to Georgia. In the classroom of my new school is an Apple ][+. I am a fan of video games and am eager to use the Apple to make one of my own. I ask about it almost immediately. And my hopes are dashed as I am told students must complete an introductory class before being allowed to use it and they will not be having another one until next year. Thinking fast, I tell Ms. Torbush that I already had that class at my old school so no problem. She believes me.

That afternoon before going home I steal the manual for the Apple. I read it cover to cover at least twice that evening, re-reading some sections several times. I am fascinated. I return the manual the following day, unnoticed. After lunch Ms. Torbush sits me down at the Apple ][+ and I impress her with my knowledge. I am given extra computer privileges.


Bored in the summer I start BBSing on a TI terminal in my mother’s office at Fort McPherson, Georgia. It uses a 300 baud acoustic coupler modem and has no display–everything is printed onto thermal paper. The phones are rotary dial. I spend hours on it by myself in an empty office, with thermal paper strewn everywhere, hip high.

For my tenth birthday I get my first computer, a Commodore VIC-20. And almost immediately get a Vicmodem so I can continue BBSing.

Long distance is still very expensive at this point, most places you have to pay (a lot!) to call even one town over. But in the Atlanta metro area–home of Georgia Tech, Hayes Microcomputing, etc–the entire 404 area code is considered a local call. This results in a thriving BBS scene.


Once again it’s summer and I am bored at my mother’s office, this time at Fort Sheridan, Illinois. It’s a Sunday, no one is around except me and her. She’s busy working. I start goofing around with a terminal connected to the base’s main computer (never did know what it was). I found the admin mode and decided to have some fun. At the time people called me “Jay” so I put “Hi from Jay!” up on the display of the terminal window and set up a triple bucky key combination to dismiss it. I believe this is friendly and that the person whose terminal it is will figure it out in a couple of minutes, like I would have, and laugh.

We go home.

On Monday folks arrive to work, including the base commander, and every terminal is locked up, displaying the message “Hi from Jay!”

They figure out right away who it is. But do they call the school and ask me to help? No, it is a national security incident; they are not interested in my help. An incident response team is flown in from the Pentagon.

My mother is not fired but I am banned from Fort Sheridan for life.


I start operating the WOPR BBS on a TRS-80 Model III at 300 baud. It is popular enough I am able to charge money for premium access. I run Eric Greene’s The Greene Machine software, which I customize and add to significantly. I receive a hand-me-down Hayes Smartmodem 1200 when a fellow BBS operator receives a Smartmodem 2400 beta unit. I discover my first security flaw; it allows me to work out internal user IDs on other boards. This information was sensitive because the community was small and passwords were stored in the clear. Passwords were also printed in logs and some boards had multiple operators. Most people didn’t have unique passwords, so keeping that internal user ID private was key.


An FBI agent shows up asking questions about pirated software and phreaking, makes noises about confiscating my computer. My mother tells him off, says I am a minor, the computer belongs to her and slams the door in his face. That is the end of it–they don’t have laws to deal with this.

A guy in my neighborhood named Lon Bush, who works at Delta Airlines, digs a Honeywell minicomputer, disk drive unit and several terminals out of a Dumpster at the Atlanta airport and gives it all to me. It is part of the old APOLLO reservation system that Delta is replacing. It is large and it works, but there are no developer tools so it’s pretty boring. It does, however, make my bedroom–I’d already moved the bed out and replaced it with a sofa–look totally badass. Boz from Riptide has nothing on my setup.


I return to Ms. Torbush’s classroom to be a teacher’s aide for a day as part of some school program. There not being much for me to do I sit down at the old Apple ][+ and by the end of the day have written a pretty sweet drawing program with multiple line widths and color selection.

The children in the class ridicule me mercilessly.


I write Geometry textbook companion software designed by my teacher, it generates unique tests for each student to deter cheating.


I am hired as the ostensible Mac expert at an Amiga store. I sell Caligari and Video Toasters.


I work in the Staples Direct call center. I discover the AS/400 terminals in the training room are much more open than the ones on the floor and I am able to read through all its documentation. From there I find a way to enumerate accounts. I spot one called SDRGEN – Staples Direct Report Generator. I decide this sounds like an account with elevated privleges used by clerical workers to generate reports. First password I try: SDRGEN

I’m in. The account is a completely unrestricted admin account, despite the quite granular permissions I’d read about in the manual. I can connect as admin remotely to other systems, too. Folks know I have admin access–my boss has me approve returns above his authorization level on weekends. I keep the access until I leave the job.


I start my first tech company, working on augmented reality. It is, alas, a bit too early for AR. Our salesman at Silicon Graphics is crushed.


I am the IT Director for a group of medical clinics and a reference diagnostic lab. Our laboratory information system (LIS) is down but must be up when the phlebotomists arrive at 5a or tests aren’t going to run and people could die. It’s 3a, I am unable to leave and re-enter the building due to the security system. I put together a solution but need an Ethernet crossover cable to implement it. With no tools and unable to leave, I use my teeth to chew through the outer insulation and strip the necessary wires. I twist them together and wrap some Scotch tape around it. The system comes up.


I am an Internet backbone engineer at Worldcom–our offices formerly the home of UUNET, AOL, AOL Advanced Networks, MCI WorldCom Advanced Networks, MCI and CompuServe. Worldcom’s network is now larger than its next six competitors–Sprint, AT&T, Qwest, etc–combined. We literally have WorldCom Borg desktop backgrounds.

My team (and our counterparts in Virginia) are the senior engineers responsible for the day-to-day operations of most of the Internet at that time. We also run non-Internet networks such as Visa’s VITAL network, CompuServe’s old PDP-10s, pager networks, ancient X.25 networks used by banks that bank IT people are scared to touch, the dial-up modems located in POPs around the country that served MSN, AOL, Earthlink, you name it. Did it always seem like the busy signals were the same no matter which ISP you switched to? Yeah, well, they were. And we didn’t have any way to provision capacity granularly, so MSN couldn’t buy more modems than Earthlink–we just didn’t have the ability to do that.

We are still in pager days, but pager subscriptions are not all created equal. Regular schmoes buying a pager get Priorty 5 service. Physicians, firefighters, police receive Priority 4 service. As you can imagine, this means that in the case of network congestion P4 pages are delivered before P5 pages. Priority 3 service is for members of Congress, state governors, generals and similar. Priority 2 service is for the Joint Chiefs of Staff, National Security Council, the Vice President and folks like that. Priority 1 service, you see where this is going, is for the President of the United States. But there is also a sixth level of service, Priority 0. Priority 0 pagers are carried exclusively by my team and our counterparts in Virginia. As we are responsible for the networks themselves pages to us are considered higher priority than pages to the president.

December 31, 1999 I’m the senior technical staff member onsite at the Hilliard NOC, ready to save the Internet from the Y2K bug. This mostly consisted of drinking champagne and pranking the outside Y2K consultants who’d set up a “war room” in our training area. They had a number of dashboards set up on different monitors, which we notice right away are frozen. We stop by every once in a while and ask them how it is going, they check their frozen dashboards and give us thumbs up. We play red alert sirens through the training computers, give them all kinds of hell.

It’s midnight in New Zealand. We receive panicked reports that phones are out. It seems thousands of customers are all checking for dial tone right at midnight, but since POTS switches are always oversubscribed some of them do not find it.

I form WorldCom’s Router Operations Center managed services group, wrangling the consolidation of managed CPE product support from diverse groups throughout the company.

The world’s largest network contract–$10,000,000/month for Internet and VPN connections across all of Toyota, a handshake deal between the CEOs–has hit a brick wall the night before it is supposed to go live. I am on my way home, having prepared a class on the hardware related to this project. I hear the implementation team arguing down the hall, I ask what’s up. They tell me they are having trouble bringing up a switch for the Toyota project and aren’t going to be able to deliver on time. I offer to help. They laugh politely. I explain that I just wrote a class on this switch and they tell me to proceed. They watch over my shoulder, it bugs me, so I tell them I am giving up. They tell their boss the project is not going to deliver on time and go home. I grab a burger and a beer then dial in to one of the errant switches. By 9p I have it all working. I call the manager of the implementation team and inform him we are not going to disappoint Toyota.

I receive a personal attaboy from Bernie Ebbers.

This puts me on a VP track and I am tasked with a new project automating management of a large chunk of the Internet, but startups are where I want to be.


I am the Principal Engineer at a startup, CSA, that’s won the contract to do all of Bellsouth’s DSL installs. We’re using that contract to fund my first product, a managed security service. This is before the term Software as a Service has been coined. We give the customer a hardware firewall for free and charge them a subscription fee to manage it.


Following an industrial sabotage issue resulting from a security breach and the CEO’s subsequent decision to not implement my plan to wipe all affected machines, CSA (now with offices in multiple cities) starts massive layoffs. I am not laid off but out of the blue I am offered a job by indie rock promoter (and, later, BB King manager) Chris Zahn promoting shows at Wetlands Preserve and CBGB in New York City.


Full of confidence now that I have worked with so many successful creative people in New York I decide to leave tech behind and return to college to study English and become a writer. I am aware studying English isn’t necessary to be a writer, but I figure being enrolled in classes full time will give me more time to write. I meet my future wife, April. I take a job at Jimmy Buffett’s Margaritaville Store–I’m supposed to be a clerk but they let me spend most of my time on process improvement. By the time I leave they don’t need to hire a replacement due to increased efficiency.


Our first child is born and I take a job managing systems at the University of Pennsylvania’s Linguistic Data Consortium. The LDC is doing early ML research and operating at startup speed with fast-moving projects that the School of Engineering is sick of supporting. I build out a large-scale storage and cloud infrastructure that works so well we start providing storage and computer services to other research facilities around the world. I design and implement a gnarly but functional petabyte-scale global filesystem using NFS, symlinks, rubber bands and chewing gum. It has advanced features like customized views into the file system for different projects–this is originally to support legacy tools with hardcoded paths, but it evolves into a way of curating project data.

I write our backup software, including a driver for the tape library robot, as there is no commercial system on the market that can handle our performance requirements. I write a data center automation system so new servers can just be plugged in, identified (storage, compute, etc), automatically configured and their services made available instantly.

This is all prior to the launch of AWS.

I also–with help of DNS wizard Bill Clark–design and implement all of the routers and firewalls, even invisible bridges to handle delicate situations where slow-moving university rules have not quite caught up to our needs.

Data distribution is a big part of the LDC and we send out a lot of data on hard drives. Our hard drive duplicator was slow, expensive and handled three drives at a time, but now it is broken. I build a much faster system that handles sixteen drives at a time out of spare parts we have lying around.


I go to work for Kodak Gallery in Emeryville as a Storage Engineer. I go through several weeks of training in the dark arts of manual processes they use to manage several petabytes on bare metal spread out in data centers across the world. It is stuff like “copy the full-page output of this GUI program, then paste it into a sed command in the console, copy the results of that and ssh into…”. I take all my notes in pseudocode, turn that into Ruby and integrate it into a Rails app. Our primary storage clusters are Isilon (FreeBSD) and only officially manageable via a Windows GUI. But while working on an issue with their support team they ask me to run some undocumented commands, thus revealing they have ways of managing via CLI. I pester them until they give up the full list of commands and thus I am able to automate the management of those clusters.

I decide at this point the future of operations at scale will be collapsed into cloud service providers, that I should either try to become one of the few people who will have ops jobs at scale in the future or move on. Indeed, my old storage team at Kodak Gallery is bought by Savvis after I leave.


I join FieldReport, my first VC-funded Bay Area startup. We are building a Rails app hailed as the American Idol of blogging, with a $1,000,000 prize for the best true story as determined by voting and a clever algorithm. I am quickly promoted to CTO where I recruit, hire and lead a truly wonderful and amazing team.

The economy tanks.

For the next few years I bootstrap over a dozen startup products while doing consulting work. I make app.lianc.es, a pre-Docker approach to containers and scaling built with FreeBSD jails and git. Thanks to FreeBSD’s clean design it is easy to make fully composable. Opengator is a crowdsourced investigative journalism app for people who love mysteries–why watch Law & Order when you can do it? There are some privacy concerns with the project, unfortunately.


I meet with a prospective client and realize I am inadvertently in the middle of a job interview. But it’s OK, we get along and I am interested in the work. I handle product management for MGM, Fox, Jessica Simpson, CBS, Boise Cascade and Brand Sense Partners. I build a container + configuration management system that scales on the fly to manage the bursty nature of product licensing management traffic.

Fuzz Leonard